


Maybe a Hundred Times Before

by coffeeinallcaps



Category: Teen Wolf (TV)
Genre: Blowjobs, Derek is bossy in bed, Explicit Sexual Content, First Time, M/M, Porn Without Plot, Smut
Language: English
Status: Completed
Published: 2012-12-15
Updated: 2012-12-15
Packaged: 2017-11-21 05:36:32
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,700
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/594048
Author URL: https://archiveofourown.org/users/coffeeinallcaps/pseuds/coffeeinallcaps
Summary: <blockquote class="userstuff">
              <p>The first time it happened was after movie night at Derek’s.</p>
            </blockquote>





	Maybe a Hundred Times Before

The first time it happened was after movie night at Derek’s. The Hale mansion – though mostly renovated – was still empty and huge, the heating not working properly yet. Weary of staving off the alphas earlier that day, everyone had huddled closely together on the couches to watch _X-Men_. It was only a matter of time before the tiredness and the werewolves’ body heat and the familiar sounds of a movie he knew by heart lulled Stiles to sleep.

He woke up to a warm body pressed to him from behind and a hand trailing up and down his side. It wasn’t quite petting, not quite tickling; Stiles could feel the edge of nails through the fabric of his T-shirt and the pressure of a thumb stroking down the ridges of his ribs, one by one by one until the hand reached the most sensitive stretch of his skin, inching down to ghost across his hipbone and then slowly back up to start the pattern anew. Every time, the hand reached a little bit lower. Once, it bumped against the waistband of his boxers and paused there for a long second before sliding up again.

Stiles knew it was Derek, could tell from the broadness of his chest and the deepness of his breath and the precision of his touch. He didn’t move except to blink open one eye. On the television screen, the movie credits were rolling; the room was dark and the other couches empty. Everyone else was gone. Stiles wondered briefly what time it was, but then Derek’s hand dipped down again and his stomach somersaulted, a warm prickling sensation spreading out from Derek’s fingers to every single part of his body, and all he could focus on was staying as still as possible so Derek wouldn’t stop.

On its next way up, Derek’s hand upset Stiles’ T-shirt slightly and his fingers brushed across bare skin instead. Stiles couldn’t help it—he took in a sharp breath, loud in the quiet room.

Derek stilled.

 _Don’t stop_ , Stiles mentally yelled at him. _Don’t stop touching_. He shifted a little, not quite onto his back but enough to offer more of his abdomen to Derek. His heart was beating unbearably loud in his ears.

After a few excruciating seconds of silence and stillness, Derek’s hand started moving again, under Stiles’ shirt this time. His fingertips were warm and callused and Stiles had to bite down on the inside of his bottom lip to stop from arching into the touch. Derek was a tactile person, he used hands more often than words to overpower or comfort someone but this, this was different. Nothing like this had ever happened before, and Stiles wasn’t going to be the one to ruin it.

Derek’s fingers moved up, stroking, exploring. Stiles’ eyes slid shut when they happened upon his nipple. He shifted again so the hand could slide to his other nipple and then down again, down the middle of his chest, the slight dip under his ribcage, his belly button, the trail of hair leading into his boxers. That’s where Derek stopped, two fingertips hooked under the waistband.

 _More_ , Stiles pleaded in his mind. _Give me more_. He became aware of Derek’s breath against the skin behind his ear, quicker and shallower than before. Stiles let out some sort of… noise – something in-between a sigh and a moan – that made his face heat up. Derek’s mouth was pressed to the base of Stiles’ neck as his hand slid into Stiles’ boxers and gripped his mostly hard dick. The pulsating warmth in Stiles’ stomach spiked and he kind of sigh-moaned again, reaching down with one hand to pop the button of his pants to facilitate access.

Derek’s hand was larger than his own, warmer, the skin rougher and the fingers broader. This was completely different from when Stiles jerked himself off; he had no idea what Derek was going to do, how tight the next stroke was going to be, what the rhythm was going to be like. It was at once infuriating and ridiculously sexy. Derek was breathing hard by now as his fist moved up and down Stiles’ dick, tight and hot and fast. On the next upstroke, his thumb rubbed heavily across the head. Stiles’ eyes shot open and he whispered, “ _Oh_ ,” into the dark room.

It was more of a groan than an actual word; still, it was the first word either of them had spoken. Derek’s hand started to slow down, but Stiles couldn’t stop anymore. He didn't want this to stop. It was too late, this was happening, Derek was touching his dick and he was already so close. He writhed a little and bucked up into Derek’s hand, whispering – whispering _something_ , God, he didn’t even know what, maybe “C’mon,” or “Yeah,” or “Fuck,” or even “Derek,” but Derek got the message and continued to stroke him relentlessly until Stiles’ brain flat-lined and he felt himself come into Derek’s palm and on his own abdomen with a stilted cry.

Derek wiped his hand on the inside of Stiles’ boxers and let it linger there, kind of cupping Stiles’ softening dick and stroking the curls of hair around it with the pad of his thumb. And Stiles, Stiles was pretty sure that this was the moment to be freaking out but he felt hazy and sated and little spikes of pleasure were still smoldering in his stomach, so instead he did the more logical thing and fell back asleep.

 

* * *

 

The second time was after the alpha pack attacked. Naturally, Stiles had disregarded Derek’s order for him to stay out of the crossfire, and with good reason; Isaac would have gotten himself impaled on a tree branch if Stiles hadn’t swept in to save the day.

“You’re an idiot,” Derek grumbled, depositing Stiles on the toilet seat and turning his broad back to him. “Where do you keep medical supplies?”

“Bottom drawer on the left.”

Stiles watched Derek rifle through the medicine cabinet. His tank top was so ripped and blood-stained it could barely even be considered a shirt anymore.

“Oh, and by the way, fuck you,” Stiles said conversationally. “I totally saved his ass.”

“Yeah, and look where it got you.”

“It’s just a flesh wound!” Stiles protested, turning his head awkwardly to investigate the claw marks on his chest. It really wasn’t that bad; the scratches weren’t deep at all and the bleeding had already stopped. He’d contracted worse injuries on the lacrosse field. “You’re being a drama queen.”

“You’re an idiot,” Derek said again and kneeled in front of Stiles, pushing his legs apart.

“Um,” Stiles said.

Derek pulled up one eyebrow at him and started to dab at the wounds with a wet cloth. Stiles was too preoccupied with other things – like the way Derek’s free hand was squeezing the inside of his thigh, or the intense scowl of concentration on Derek’s face, or the fact that Derek was _kneeling between his legs and touching his naked chest_ – to really register the sting. He watched as Derek washed away the blood and stuck an adhesive dressing on him.

“There you go,” Derek said, tracing the edges of the dressing with his fingertip. The thumb of his other hand was drawing circles against Stiles’ inner thigh.

Stiles opened his mouth to say ‘thank you’, but the sound that came out was closer to, “Hngh.” (In his defense, it had been two weeks since Derek had given him a handjob and then disappeared, proceeding to not to talk about it or act like anything had ever happened, to the point where Stiles had almost started to believe that it had been nothing but a particularly vivid spasm of his imagination. And now _this_.)

Derek looked up and their gazes locked. The hand on Stiles’ chest flattened over his heart; Derek’s other hand came up as well. Stiles’ own hands curled into loose fists. Derek started to touch him, tracing the edges of Stiles’ collarbone and his shoulders, tickling down his upper arms and then back to his chest, brushing across his nipples, his abs, squeezing his hipbones. Stiles tried not to move but he just _had_ to lean back when Derek’s hands slid around and dipped into his jeans. The bathroom tiles were impossibly cold against his naked back, and a full-body shudder came over him.

Derek chuckled.

 _Shut up_ , Stiles wanted to say, but then Derek leaned down and mouthed at his hardening dick in his jeans and instead he just swallowed, thickly. Derek pushed both hands into the V of Stiles’ legs to make him spread them wider. He undid the button and lowered the fly with his teeth.

“Hngh,” Stiles said again, watching Derek lick and nose at his hard-on through the cotton of his boxers. Derek sucked the tip into his mouth, and although Stiles had never been on the receiving end of a blowjob before (nor on the delivering end, but whatever) he was pretty sure the boxers were supposed to go. Not that he was complaining, because this was already making his toes curl, but still. He lifted his hips, and together they pushed his jeans and boxers down to pool around his feet.

Derek licked up and down the entire length of Stiles’ dick and mouthed at his balls before wrapping his lips around the head, and by that time Stiles felt sufficiently wrecked. The back of his head ached (had he hit it against the wall?) and he had to dig his nails into his own palms to stop from grabbing Derek’s hair. He was pretty sure the entire pack was still downstairs, and he had no idea how far their hearing actually reached, and his dad was due to come home sometime during the next hour or so, but it was hard to care about any of that when Derek’s eyes were slipping shut and he was making content little noises as he sucked Stiles off. Fuck. The contours of Derek’s stubble made his cheeks look even more hollowed; beneath it, his face was flushed red.

“Can I—” Stiles panted, and threaded his fingers through Derek’s hair without awaiting approval. Derek blinked up at him with heavy-lidded eyes. He pulled off and for a split second Stiles worried he had made a faux pas, but Derek just brought his own hand up to his mouth and, Jesus, started to perform fucking fellatio on it.

“Have you ever done this to yourself,” Derek asked after taking his slicked-up fingers out of his mouth. His voice sounded rough and deeper than normal.

 _What, blown myself? That’s impossible_ , Stiles thought in reply, but then he felt a wet probe in-between his legs and, oh. _Oh_. He opened them wider and nodded possibly a little too enthusiastically, because Derek grinned and asked, “Yeah?” before closing his mouth around Stiles’ dick again and simultaneously pushing two fingers in at once.

“Oh Jesus,” Stiles moaned, sliding both of his hands into Derek’s hair. “ _Fuck_.”

The angle felt much better when someone else was doing it, and he was pretty sure Derek had found his prostate in one go because his entire body convulsed with how great it felt. Which was somewhat embarrassing, but Derek just hummed again and started fingering him, sliding his fingers in and out again. His lips were still wrapped around Stiles’ dick, Derek’s other hand cupping his balls, and it was too good, too much, too _everything_. Stiles had to close his eyes. He tugged at Derek’s hair and gave up all attempts of keeping the sounds in. He was moaning, actually moaning, long loud noises that made Derek press his fingers back in even harder, and when he came in Derek’s mouth it was the best orgasm he’d ever had.

 

* * *

 

The third time it happened was at Scott’s house. The alpha pack had targeted the Hale mansion two days before, and Derek deemed it too dangerous for their own pack to be scattered across Beacon Hills. Scott’s mother was on night shift; Derek had laid claim to Scott’s bed, and the others had brought airbeds to camp out in the living room.

Once everyone was asleep, Stiles slid out of his sleeping bag and sneaked up the stairs. Derek was lying on his side with the blankets pooling around his waist. He must have heard Stiles – Derek was ever vigilant, especially now – but he didn’t move when Stiles crawled into the bed and tucked himself against his back.

“You awake?” he whispered, because it wasn’t really his style to fondle anyone in their sleep, much less an alpha werewolf with deep-rooted trust issues.

“Yeah,” Derek murmured back.

“’kay.” The skin of Derek’s bicep was warm, muscles thick and hard even when slack; his abdomen felt ridiculously contoured. Stiles pressed a kiss to the tattoo between Derek’s shoulder blades as he took hold of his dick. It was thicker than his own, only half-hard now but rapidly becoming harder in his grip. Stiles traced his fingers around the head, light experimental touches. Derek groaned low in his throat.

Stiles set a quick rhythm, drawing on his memory of Derek jerking him off on the couch for reference. It wasn’t much different from touching himself, except it was harder to tell what was working and what wasn’t; he had to rely on little signs like the loudness and the pace of Derek’s breathing or the way his hands clenched and unclenched into the pillow. When Stiles gripped tighter, Derek hummed and rolled up his hips to meet Stiles’ fist. Stiles circled his thumb around the head of Derek’s dick, squeezing slightly.

“Fuck,” Derek muttered, thrusting up into Stiles’ hand again. “Fuck, Stiles, that feels good.”

Stiles had never heard his name said that way before. He already wanted to hear it again. He shuffled closer, his own clothed erection pressing between Derek’s ass cheeks, and bit down on the slope of Derek’s shoulder.

“ _Stiles_ ,” Derek murmured, tilting his head back. Stiles let his teeth dig in a little longer and sucked a mark into Derek’s skin. It would fade soon enough, but it was the thought that counted. “Stiles,” Derek moaned again, the second ‘s’ dissolving into a quiet moan as he came.

 

* * *

 

The fourth time it happened was after they had taken down the alpha pack. Erica and Scott had both been injured badly, and although they’d healed quick enough it was hard to forget about the sight of their blood-soaked bodies. Worse still was the mental image of the dead alpha female. Stiles knew it had either been one of theirs or one (or worse, several) of their own, that there had been no other way to make the alpha pack stop. But in death, the eyes of the woman – the _girl_ , she was just a girl, not that much older than Derek – had looked so feral yet so empty at the same time, and their stare was painted on the backs of his own eyelids.

Which was why he found himself breaking the speed limit on his way to the Hale mansion at five in the morning. Derek always locked the doors, despite the fact that a simple lock would not stop anyone or anything truly dangerous to break into the house (Stiles guessed it was more of a psychological thing), but Stiles knew where to find the key. He let himself in, took the stairs two at a time, and practically ran into the master bedroom.

Derek’s arm muscles rolled and flexed as he pushed himself into an upright position. His hair was messy. He didn’t look surprised to see Stiles at all.

“I need you,” Stiles said as he kicked away his sneakers, ripped off his shirt, and kind of launched himself onto the bed. “I need you to touch me, I need—”

Derek grabbed him by the shoulders and flipped him onto his back, covering Stiles with his entire body. He was everywhere, engulfing Stiles in body heat and the smell of aftershave and sleep and, vaguely, leather. Derek’s underarm pressed down painfully on Stiles’ sternum as he nipped and sucked at Stiles’ neck. Stomach jolting, Stiles dragged his nails down Derek’s back, hard, and thrust his hips upward.

“Derek, please, I—”

Derek reached into his sweatpants and started to jerk him off roughly, sloppily. Stiles met him on every downward stroke, his spine arching away from the mattress. He closed his eyes and focused on the overwhelming feeling. When he opened them again, Derek was staring at him with dark eyes. Stiles reached out one hand and curved it around Derek’s jaw, stroking the stubble there with his thumb. Derek pressed their foreheads together. He palmed the head of Stiles’ dick, not breaking eye contact.

“More,” Stiles said, voice rough. “Derek, I want more.”

Derek studied his face for a few seconds before nodding and letting go. He got off the bed. Stiles sat up, tried to catch his breath as Derek rummaged through a drawer and came back with a condom and a tube of lube.

“This is your first time,” Derek said, kneeling on the bed. It wasn’t a question, but if Stiles had been asked to pinpoint one in the words anyway, it would’ve been _are you sure?_ He nodded.

“Turn around. Get on your knees.”

Stiles complied. Derek pushed and prodded at him and rearranged them until Stiles was naked on all fours with his head down between his elbows, one of Derek’s hands at the base of his neck and the other pushing in two fingers. Stiles shivered at the coldness of the lube. Derek stopped. Stiles pushed back to make the fingers slide in farther, to the knuckle. “More,” he said, again.

Derek slipped in a third. “Touch yourself,” he demanded, other hand flexing around Stiles’ neck. Stiles obediently fondled his dick, but it was difficult to focus while Derek was fingering him, his breath making the skin of Stiles’ back erupt in goose bumps.

“ _Derek_ ,” Stiles said, whined almost. “Enough.”

Derek pulled his fingers out and thrust them all the way back in. Stiles moaned.

“Seriously,” he said. “I’ve been practicing.”

With a breathy laugh, Derek said, “My dick is bigger than your vibrator.”

“Whoa, all right then, Mr. Confident. I’m not even going to ask you how you even know that.”

The light-hearted banter made Stiles feel less nervous as Derek slid his fingers out of him and tugged his hips up higher. Stiles’ face was smushed onto his forearm now, his naked body curved almost like a triangle. He felt awkward, exposed, but it was also kind of a turn-on to know that Derek wanted him like this. He swallowed at the sound of the condom wrapper being ripped open, the sound of rubber being rolled on.

“You good?” Derek asked, steadying Stiles with a hand on his hip. Stiles felt something nudge inside, but it was only Derek’s thumb, the line of his hard dick pressing between Stiles’ ass cheeks.

“ _Yes_ ,” Stiles said.

Derek’s thumb slipped out again and Stiles felt the tip of his dick settle against his hole. He breathed out and relaxed, but Derek paused again. “Tell me what you want,” he said.

“Oh my God, _Derek_ ,” Stiles half-yelled. “I want you to fuck me, okay? Just do it.”

The head pressed in. “Why me,” Derek asked in a strained, breathless voice.

“Because you’re _you_ ,” Stiles said, and it wasn’t much of an explanation but Derek seemed to accept it as one, his hand settling on Stiles’ neck again as he sank inside. It didn’t hurt much, only the last inch or so, and Derek stayed still for so long to let Stiles accommodate that it was almost unbearable.

“C’mon,” Stiles said, lifting his ass even higher. “Derek. C’mon.”

Derek chuckled and pulled out almost all the way before pushing back in. The drag of his dick inside Stiles was almost excruciatingly slow, the spark of pleasure at the end as it hit his prostate intense but too brief.

“ _Dude_ ,” Stiles said, reaching back with one hand to touch Derek somewhere, anywhere. He settled for a butt cheek and pinched it, hard. “I’m not made of fucking glass.”

“Not doing this,” Derek panted, pulling back again, “to be careful.”

Stiles moaned. “Why—”

“Because it feels good,” Derek said, thrusting in hard this time. Stiles felt it all the way into his toes. He swore and squeezed his eyes shut, reaching for his dick, but Derek’s hand closed around his wrist. “Don’t.”

Their fingers entwined, and Derek finally started fucking him harder, deeper. Stiles could feel him slowly lose himself, lose control, could feel it in the quickening of his thrusts and the scrape of stubble against his back and the way Derek was holding his hand so tightly Stiles was afraid it would fall off. It was hot, and after a few last uncoordinated thrusts Derek stilled and moaned lowly as he came, which was so fucking hot that Stiles honestly went light-headed for a few seconds. Derek pulled out, but before Stiles could mourn the loss of his dick he was flipped onto his back again and Derek’s mouth was closing around his dick, three fingers sliding into him.

“Fuck, Derek, _Derek,”_ Stiles moaned, fisting his hands into Derek’s hair and pushing up into his mouth, “ _Derek_ ,” and then he was coming.

Derek swallowed his come and lapped at his dick. Stiles had to close his eyes for a few seconds. He heard Derek pull off the condom, rustle off the bed. Footsteps padding across the room. Toilet flushing. Footsteps padding back into the room. Halting at the bed. Stiles peeked through his eyelashes and saw Derek pick up a pair of – he couldn’t see what they were, jeans maybe, definitely not sweatpants. His throat constricted a little. So far, he suspected, Derek had always left or disappeared straight afterward.

Without allowing himself to think about it twice, Stiles rolled over and wrapped a hand around Derek’s wrist. “Don’t go,” he mumbled, heart pounding.

Derek looked at him. Then he said, “All right.”

In the morning, they kissed for the first time.

**Author's Note:**

> Thank you for reading! I'm also [on Tumblr](http://coffeeinallcaps.tumblr.com/).


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